EP3024898A1 - Eingekapselte katalysatoren - Google Patents
Eingekapselte katalysatorenInfo
- Publication number
- EP3024898A1 EP3024898A1 EP13744778.5A EP13744778A EP3024898A1 EP 3024898 A1 EP3024898 A1 EP 3024898A1 EP 13744778 A EP13744778 A EP 13744778A EP 3024898 A1 EP3024898 A1 EP 3024898A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- group
- heteroaryl
- independently selected
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title description 23
- 239000003973 paint Substances 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000008199 coating composition Substances 0.000 claims abstract description 42
- 229920000180 alkyd Polymers 0.000 claims abstract description 36
- 229910052742 iron Inorganic materials 0.000 claims abstract description 28
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 C2-6-alkenyl ether Chemical compound 0.000 claims description 149
- 239000000243 solution Substances 0.000 claims description 88
- 239000003446 ligand Substances 0.000 claims description 87
- 239000002904 solvent Substances 0.000 claims description 87
- 125000001072 heteroaryl group Chemical class 0.000 claims description 66
- 238000001035 drying Methods 0.000 claims description 62
- 238000002156 mixing Methods 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 238000000576 coating method Methods 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- 239000011248 coating agent Substances 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000004429 atom Chemical group 0.000 claims description 37
- 239000003094 microcapsule Substances 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 28
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000000839 emulsion Substances 0.000 claims description 25
- 239000012948 isocyanate Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 24
- 150000003077 polyols Chemical class 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 150000002513 isocyanates Chemical class 0.000 claims description 23
- 229920005862 polyol Polymers 0.000 claims description 23
- 125000002883 imidazolyl group Chemical group 0.000 claims description 22
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 22
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 22
- 229910052723 transition metal Inorganic materials 0.000 claims description 22
- 125000001425 triazolyl group Chemical group 0.000 claims description 22
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 21
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 21
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000001041 indolyl group Chemical group 0.000 claims description 21
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 21
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 21
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 21
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 21
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 21
- 125000000335 thiazolyl group Chemical group 0.000 claims description 21
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 21
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000004814 polyurethane Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229920002635 polyurethane Polymers 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 150000003624 transition metals Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229920002396 Polyurea Polymers 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 10
- 229910052720 vanadium Inorganic materials 0.000 claims description 10
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 8
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
- 229910052726 zirconium Inorganic materials 0.000 claims description 8
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052684 Cerium Inorganic materials 0.000 claims description 7
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 229910052788 barium Inorganic materials 0.000 claims description 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052712 strontium Inorganic materials 0.000 claims description 5
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 5
- SDNGAOSFCJYACN-UHFFFAOYSA-N 1,1,2-tripyridin-2-ylpropan-1-amine Chemical compound N1=C(C=CC=C1)C(C(N)(C1=NC=CC=C1)C1=NC=CC=C1)C SDNGAOSFCJYACN-UHFFFAOYSA-N 0.000 claims description 4
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims description 4
- ANFHBNXMBQROBX-UHFFFAOYSA-N 2-phenyl-1,1,2-tripyridin-2-ylpropan-1-amine Chemical compound N1=C(C=CC=C1)C(C(N)(C1=NC=CC=C1)C1=NC=CC=C1)(C1=CC=CC=C1)C ANFHBNXMBQROBX-UHFFFAOYSA-N 0.000 claims description 4
- FGVBSRHTSFUPNH-UHFFFAOYSA-N 4,11-dibenzyl-1,4,8,11-tetrazabicyclo[6.6.2]hexadecane Chemical compound C=1C=CC=CC=1CN(CCN(CCC1)CC2)CCCN2CCN1CC1=CC=CC=C1 FGVBSRHTSFUPNH-UHFFFAOYSA-N 0.000 claims description 4
- NJMWXCOSLAUOGE-UHFFFAOYSA-N 4,11-dimethyl-1,4,8,11-tetrazabicyclo[6.6.2]hexadecane Chemical compound C1CN(C)CCCN2CCN(C)CCCN1CC2 NJMWXCOSLAUOGE-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical class 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- LVQMWOWPMUXJJQ-UHFFFAOYSA-N dimethyl 3-methyl-9-oxo-2,4-dipyridin-2-yl-7-(pyridin-2-ylmethyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate Chemical compound C1C(C2=O)(C(=O)OC)C(C=3N=CC=CC=3)N(C)C(C=3N=CC=CC=3)C2(C(=O)OC)CN1CC1=CC=CC=N1 LVQMWOWPMUXJJQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- KGGVGTQEGGOZRN-PLNGDYQASA-N (nz)-n-butylidenehydroxylamine Chemical compound CCC\C=N/O KGGVGTQEGGOZRN-PLNGDYQASA-N 0.000 claims description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 3
- PRICLFAUAJHZLI-UHFFFAOYSA-N 1,1-dipyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(C(C=1N=CC=CC=1)C=1N=CC=CC=1)CC1=CC=CC=N1 PRICLFAUAJHZLI-UHFFFAOYSA-N 0.000 claims description 3
- NVFSHTYUVXEYKP-UHFFFAOYSA-N 1,4,7,10-tetrakis(pyridin-2-ylmethyl)-1,4,7,10-tetrazacyclododecane Chemical compound C=1C=CC=NC=1CN(CCN(CC=1N=CC=CC=1)CCN(CC=1N=CC=CC=1)CC1)CCN1CC1=CC=CC=N1 NVFSHTYUVXEYKP-UHFFFAOYSA-N 0.000 claims description 3
- STYFDKOQURBOGQ-UHFFFAOYSA-N 1,4,7,10-tetramethyl-1,4,7,10-tetrazacyclododecane Chemical compound CN1CCN(C)CCN(C)CCN(C)CC1 STYFDKOQURBOGQ-UHFFFAOYSA-N 0.000 claims description 3
- HRFJEOWVAGSJNW-UHFFFAOYSA-N 1,4,8,11-tetramethyl-1,4,8,11-tetrazacyclotetradecane Chemical compound CN1CCCN(C)CCN(C)CCCN(C)CC1 HRFJEOWVAGSJNW-UHFFFAOYSA-N 0.000 claims description 3
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 claims description 3
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 claims description 3
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229960002887 deanol Drugs 0.000 claims description 3
- IMMCLGBPPSXGIZ-UHFFFAOYSA-N dimethyl 7-[2-(dimethylamino)ethyl]-3-methyl-9-oxo-2,4-dipyridin-2-yl-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate Chemical compound O=C1C2(C(=O)OC)CN(CCN(C)C)CC1(C(=O)OC)C(C=1N=CC=CC=1)N(C)C2C1=CC=CC=N1 IMMCLGBPPSXGIZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012972 dimethylethanolamine Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229920003226 polyurethane urea Polymers 0.000 claims description 3
- 239000007762 w/o emulsion Substances 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 235000010384 tocopherol Nutrition 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 238000013329 compounding Methods 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 82
- 229910052751 metal Inorganic materials 0.000 abstract description 38
- 239000002184 metal Substances 0.000 abstract description 38
- 238000009472 formulation Methods 0.000 abstract description 32
- 238000003860 storage Methods 0.000 abstract description 19
- 239000011572 manganese Substances 0.000 abstract description 15
- 229910052748 manganese Inorganic materials 0.000 abstract description 10
- 230000002829 reductive effect Effects 0.000 abstract description 9
- 229910017052 cobalt Inorganic materials 0.000 description 39
- 239000010941 cobalt Substances 0.000 description 39
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 39
- 229930195733 hydrocarbon Natural products 0.000 description 36
- 239000004215 Carbon black (E152) Substances 0.000 description 34
- 150000002430 hydrocarbons Chemical class 0.000 description 34
- 239000002775 capsule Substances 0.000 description 31
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 238000005755 formation reaction Methods 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 11
- 239000011162 core material Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000000344 soap Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 9
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical group C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 235000006708 antioxidants Nutrition 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
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- 239000001294 propane Substances 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical class [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 231100000687 reproductive toxin Toxicity 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 125000005402 stannate group Chemical group 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- VACCAVUAMIDAGB-UHFFFAOYSA-N sulfamethizole Chemical compound S1C(C)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 VACCAVUAMIDAGB-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000003741 urothelium Anatomy 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/46—Anti-skinning agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Definitions
- Methyl ethyl ketoxime and cyclohexanone oxime exhibit very similar toxic effects. For both chemicals, the major toxicity is to erythrocytes and the hematopoietic system. Each chemical causes similar lesions in the olfactory epithelium. Hyperplasia of the urinary bladder transitional epithelium was observed in mice exposed to methyl ethyl ketoxime but not cyclohexanone oxime.
- the no observed-adverse-effect level (NOAEL) for erythrotoxicity is 312 ppm in the drinking water for rats and 2,500 ppm for mice (see National Toxicology Program, Toxicity Report Series, Number 51 , July 1999, NIH
- the unsubstituted or alkyl-substituted aryl groups are the aryl groups having 6 to 18 carbon atoms such as phenyl, diphenyl and naphthyl groups, and alkylaryl groups having 7 to 40 carbon atoms wherein the alkyl group may be straight-chain or branched and may be bonded to any position on the aryl group, such as tolyl, xylyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, diethylphenyl, dibutylphenyl and dioctylphenyl groups.
- the alkylaryl groups may additionally have substituents including functional groups such as alkoxy
- the invention has broad utility in relation to a wide variety of solvent-based coating compositions, which term is to be interpreted broadly herein.
- coating compositions include clear or coloured varnishes, primary coats, filling pastes, glazes, emulsions and floor coverings, e.g. linoleum floor coverings.
- Particular embodiments of the invention relate to solvent-based paints and inks, particularly paints such as high-specification paints intended for domestic use.
- a preferred cross-bridged ligand is of the formula (V):
- each Y is independently selected from H, CH 3 , C 2 H 5 , C 3 H 7 and R18 is independently selected from an optionally substituted heteroaryl: selected from the group consisting of: pyridinyl; pyrimidinyl; pyrazinyl; triazolyl; pyridazinyl; 1 ,3,5- triazinyl; quinolinyl; isoquinolinyl; quinoxalinyl; imidazolyl; pyrazolyl; benzimidazolyl; thiazolyl; oxazolidinyl; pyrrolyl; carbazolyl; indolyl; and isoindolyl, wherein the heteroaryl may be connected to the compound via any atom in the ring of the selected heteroaryl; and at least two of R17 are -CY 2 - R18.
- the heteroatom donor group is preferably
- a first solution A was prepared by mixing 249 g dearomatized hydrocarbon solvent (ShellsolTM D60), and 6 g sorbitan monoleate (Span ® 80).
- a second solution B was prepared by mixing 99.8 g of a 4% solution of [Fe(N2py3o-C1)CI]CI (FeLT ® ) in water and 0.5 g
- a polysulfoamide shell would be formed using diamines or polyamines in the aqueous liquid and disulfonyl or polysulfonyl chlorides in the organic liquid produce a polysulfonamide capsule skin.
- a first solution A would be prepared by mixing 200 g dearomatized hydrocarbon solvent (ShellsolTM D60), and 6.8 g sorbitan monoleate (Span ® 80).
- a second solution B would be prepared by mixing 99.8 g of a 1 % solution of [Fe(N2py3o-C1 )CI]CI in water, 17.1 g of 1 1 ,6- hexamethylenediamine and 3.4 g of sodium hydroxide.
- Polyurea membranes are preferred over polyurethane formulations.
- the choice of diisocyanate also plays a role and based on initial test results, dicyclohexylmethane diisocyanate has performed well, optionally with the addition of toluene diisocyanate (TDI).
- TDI toluene diisocyanate
- the rate of mixing also plays a role. It is important in the emulsification step where must be high sheer in order to obtain small FeLT ® solution droplets. After sufficient emulsion preparation the need for high speed mixing decreases.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/GB2013/051998 WO2015011430A1 (en) | 2013-07-25 | 2013-07-25 | Encapsulated catalysts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP3024898A1 true EP3024898A1 (de) | 2016-06-01 |
| EP3024898B1 EP3024898B1 (de) | 2017-11-08 |
Family
ID=48914352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP13744778.5A Not-in-force EP3024898B1 (de) | 2013-07-25 | 2013-07-25 | Eingekapselte katalysatoren |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20160145464A1 (de) |
| EP (1) | EP3024898B1 (de) |
| JP (1) | JP2016527356A (de) |
| KR (1) | KR20160034910A (de) |
| CN (1) | CN105555881A (de) |
| AU (1) | AU2013395166B2 (de) |
| CA (1) | CA2919184A1 (de) |
| PH (1) | PH12016500175A1 (de) |
| RU (1) | RU2016105678A (de) |
| WO (1) | WO2015011430A1 (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3170847A1 (de) | 2015-11-20 | 2017-05-24 | OMG Borchers GmbH | Eingekapselte beschleuniger für beschichtungen |
| AR107070A1 (es) * | 2015-12-18 | 2018-03-14 | Catexel Ltd | Composición de recubrimiento oxidativamente curable |
| EP3272823A1 (de) * | 2016-07-19 | 2018-01-24 | ALLNEX AUSTRIA GmbH | Sikkativzusammensetzungen für alkydharze |
| EP3296353B1 (de) | 2016-09-19 | 2022-01-26 | Daw Se | Lösemittelhaltige beschichtungsmasse für lackbeschichtungen |
| EP3296372B1 (de) | 2016-09-19 | 2020-03-04 | Daw Se | Lösemittelhaltige beschichtungsmasse |
| JP7353265B2 (ja) * | 2017-08-18 | 2023-09-29 | ローム アンド ハース カンパニー | 封入触媒およびオレフィン重合方法 |
| EP3757258A4 (de) * | 2018-02-23 | 2022-01-19 | Kansai Paint Co., Ltd | Beschichtungsverfahren für kationisches elektrotauchlackmaterial |
| KR20210070334A (ko) | 2018-10-03 | 2021-06-14 | 더 보드 오브 트러스티즈 오브 더 유니버시티 오브 일리노이 | 가용화된 촉매 착물의 제조 방법, 가용화된 촉매 제제, 및 촉매 올레핀 중합의 방법 |
| CN111073459A (zh) * | 2019-12-31 | 2020-04-28 | 枣阳市旺前电泳涂料有限公司 | 一种节能环保的阴极电泳涂料 |
| JP7462756B2 (ja) | 2020-07-07 | 2024-04-05 | 株式会社巴川コーポレーション | 触媒粒子 |
| KR102474018B1 (ko) * | 2020-12-22 | 2022-12-05 | (주)엘엑스하우시스 | 인조대리석의 제조방법 |
| WO2023281046A1 (en) * | 2021-07-09 | 2023-01-12 | Umicore | Novel bispidone ligands and transition metal complexes thereof |
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| US3594666A (en) | 1968-09-06 | 1971-07-20 | Rca Corp | Gyromagnetic notch filter |
| GB2052296A (en) | 1979-05-31 | 1981-01-28 | Aocm Ltd | Raney catalyst composition |
| US4956129A (en) | 1984-03-30 | 1990-09-11 | Ici Americas Inc. | Microencapsulation process |
| DE3635822A1 (de) | 1986-10-22 | 1988-04-28 | Bayer Ag | Mikrokapseln mit waenden aus polyurethan |
| US4895994A (en) | 1988-04-14 | 1990-01-23 | W. R. Grace & Co.-Conn. | Shaped catalysts and processes |
| US5019346A (en) * | 1988-09-21 | 1991-05-28 | Ecolab Inc. | Drain treatment product and method of use |
| AU2614895A (en) | 1994-06-13 | 1996-01-05 | Unilever N.V. | Bleach activation |
| CA2257891A1 (en) | 1996-06-19 | 1997-12-24 | Roelant Mathijs Hermant | Bleach activation by an iron catalyst comprising a polydentate ligand containing at least six heteroatoms |
| WO1998028975A1 (en) | 1996-12-31 | 1998-07-09 | Zeneca Limited | Novel water-in-oil microencapsulation process and microcapsules produced thereby |
| ZA981883B (en) | 1997-03-07 | 1998-09-01 | Univ Kansas | Catalysts and methods for catalytic oxidation |
| CA2248476A1 (en) | 1997-10-01 | 1999-04-01 | Unilever Plc | Bleach activation |
| EP1115800A1 (de) | 1998-08-24 | 2001-07-18 | Akzo Nobel N.V. | Mittel zur vermeidung von hautbildung in überzügen |
| US6294571B1 (en) * | 1998-09-11 | 2001-09-25 | Independent Ink, Inc. | Method for using neem extracts and derivatives for protecting wood and other cellulosic composites |
| DE69817832T2 (de) | 1998-11-10 | 2004-10-07 | Unilever Nv | Bleich- und Oxidationskatalysator |
| AU4061900A (en) | 1999-04-01 | 2000-10-23 | Procter & Gamble Company, The | Transition metal bleaching agents |
| HUP0203723A2 (en) | 1999-12-22 | 2003-04-28 | Akzo Nobel Nv | Coating composition comprising an oxidatively drying polyunsaturated condensation product, a polythiol, and a siccative |
| GB0030673D0 (en) | 2000-12-15 | 2001-01-31 | Unilever Plc | Ligand and complex for catalytically bleaching a substrate |
| GB0102826D0 (en) | 2001-02-05 | 2001-03-21 | Unilever Plc | Composition and method for bleaching a substrate |
| US6953624B2 (en) * | 2001-03-02 | 2005-10-11 | 3M Innovative Properties Company | Printable film and coating composition exhibiting stain resistance |
| BR0211073A (pt) | 2001-07-12 | 2004-12-14 | Avecia Ltd | Sistema de catalisador, e, processos para a preparação de um catalisador microencapsulado, de bifenilas opcionalmente substituìdas, de alcenos opcionalmente substituìdos, de um produto hidrogenado e de dióis |
| WO2003029371A1 (en) | 2001-09-28 | 2003-04-10 | Akzo Nobel Coatings International B.V. | Oxidatively drying coating composition |
| EP1501906A1 (de) | 2002-05-03 | 2005-02-02 | Ato B.V. | Trockenstoff für lufttrocknende farben und lacke |
| JP2003341229A (ja) * | 2002-05-30 | 2003-12-03 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| GB0212991D0 (en) | 2002-06-06 | 2002-07-17 | Unilever Plc | Ligand and complex for catalytically bleaching a substrate |
| EP1382648A1 (de) | 2002-07-17 | 2004-01-21 | Universiteit Leiden | Sikkatif für Überzugsmittel auf Basis von Alkydharz |
| US20100233146A1 (en) * | 2002-09-09 | 2010-09-16 | Reactive Surfaces, Ltd. | Coatings and Surface Treatments Having Active Enzymes and Peptides |
| GB0319071D0 (en) * | 2003-08-14 | 2003-09-17 | Avecia Ltd | Catalyst and process |
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| DE102007033020A1 (de) | 2007-07-16 | 2009-01-22 | Universität Heidelberg | Bispidonliganden und deren Metallkomplexe |
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| JP5269917B2 (ja) | 2011-01-07 | 2013-08-21 | シャープ株式会社 | 洗濯機 |
-
2013
- 2013-07-25 EP EP13744778.5A patent/EP3024898B1/de not_active Not-in-force
- 2013-07-25 CA CA2919184A patent/CA2919184A1/en not_active Abandoned
- 2013-07-25 KR KR1020167001830A patent/KR20160034910A/ko active IP Right Grant
- 2013-07-25 AU AU2013395166A patent/AU2013395166B2/en not_active Ceased
- 2013-07-25 RU RU2016105678A patent/RU2016105678A/ru not_active Application Discontinuation
- 2013-07-25 WO PCT/GB2013/051998 patent/WO2015011430A1/en active Application Filing
- 2013-07-25 CN CN201380079630.6A patent/CN105555881A/zh active Pending
- 2013-07-25 JP JP2016528596A patent/JP2016527356A/ja active Pending
- 2013-07-25 US US14/904,765 patent/US20160145464A1/en not_active Abandoned
-
2016
- 2016-01-25 PH PH12016500175A patent/PH12016500175A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20160145464A1 (en) | 2016-05-26 |
| CN105555881A (zh) | 2016-05-04 |
| PH12016500175A1 (en) | 2016-04-25 |
| CA2919184A1 (en) | 2015-01-29 |
| EP3024898B1 (de) | 2017-11-08 |
| WO2015011430A1 (en) | 2015-01-29 |
| RU2016105678A (ru) | 2017-08-30 |
| JP2016527356A (ja) | 2016-09-08 |
| KR20160034910A (ko) | 2016-03-30 |
| AU2013395166B2 (en) | 2016-06-23 |
| AU2013395166A1 (en) | 2016-02-04 |
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